Why Rich People Love to Surf

Every surfer looks the same in the water but head to a beach right now in Malibu or Southampton, and that Sesame Street song "One of These Things (Is Not Like the Others)" might pop into your head. There's a guy rolling up to his lesson in an impossible-to-find $90,000 vintage Land Rover Defender. And there are post-surf Missoni cover-ups, hints of Rolex Daytonas gleaming in the sunlight, and flip-flops with a discreet but telltale Gucci red and green ribbon. Once the status symbols that tend to define us on land are shed, these surfers could be any of the other seals out there in black neoprene on waxed-up, dinged-up boards seeking the same rush. Surfing's equalizing force, its ability to make even the hardest--hitting titan of industry just another person battling the elements, may be one reason why a breed of one-percenters is becoming as addicted to surfing as the hippie dude in straggly hair who has always believed "blue chip" meant something you dunk into a bowl of guacamole.

Is it mere coincidence that Daniel Loeb's Third Point hedge fund is named after the farthest break off the famous Malibu pier? Or that Eva and Olaf Guerrand-Hermès are habitués of the world's most far-flung surfing locales? Music business savant Matt Pincus is known to have more surfing stamina than anyone in the waves off the Hamptons, and it's not hard to see why art dealer Adam Lindemann's Montauk retreat hangs over one of the best breaks in the East End, or to imagine the gusto with which financier and philanthropist Dirk Ziff and partners plan to expand the competitive scope, and fan base, of the World Surf League which they recently purchased.

What exactly is it about the church of surfing that gives all its disciples-—from Venice Beach surf rat to activist investor—the same mesmerized spirals in their eyes? That thrill you feel down to your toenails, whether you're carving figure eights on fresh back-country powder, hammering that drive straight through the middle of the fairway, or riding a bike down a hill for the first time in second grade—cube it, and that's where surfing takes you. I know because I've been there.

I first put my toe into the surfing world at age 40. One day, while I was jogging in the haze of an impossibly humid August, surfers teaching kids in the Atlantic and laughing out loud caught my attention, and I made a mental note to give my 10-year-old daughter a surf lesson as a gift. When the instructors took her much farther out than I felt comfortable with, I grabbed a foam board and jumped in, Mama Bear–style, and paddled after them. When I failed to make any progress amid the swirling currents, a kind instructor not only rescued me but offered to help me catch my first wave by pushing my board into the gentle swell at just the right time. Suffice it to say that that first ride, when I sort of, kind of stood up, hooked me so profoundly I could be seen in December of that year in dirty 45-degree water off Rockaway Beach, in Queens, wearing a 6mm wet suit complete with hood, face mask, booties, and gloves.

That neighborhood is populated by generations of blue-collar Irish Catholic cops and firemen who are pretty relentless about getting their waves. Changing into a wet suit on a freezing sidewalk is not something that fits my urban working-mom persona, in which I'm usually seeking the dirtiest martini, the highest heels, or the most luxurious blowout. I have since surfed in many places around the world: the Maldives, Indonesia, Costa Rica, Brazil, as well as tamer territories closer to home, including Vero Beach, Florida, and Southampton. But no matter where I've been, I've recognized more and more type A high-net-worth professionals around me.

Unlike other sports, surfing gives you no stable ground beneath your feet, no semi-predictable, immobile ski slope or mountain bike path on which you can rest and assess the steepness or figure out how to get around a tree. Once you go over the edge and commit to riding a wave, there's no way to gauge how many somersaults your body will turn if you wipe out. Without any notice at all, even the best surfers find themselves under four feet of crushing whitewater when a barreling wave suddenly envelops them from above, below, and all sides. Under all that water pressure you can't even figure out which way is up.

Someone used to getting his way by methodically climbing the ladder of success can be flummoxed by the constantly changing ocean dynamics. Food Network host and author Katie Lee, who has been surfing in Southampton for six years, enjoys witnessing those around her trying to master the sport. Most of them quickly find that surfing is a lot more difficult than acing your nemesis from Harvard Business School on the Maidstone Club's grass courts. "I try to push them to take a lesson in Southampton, where I learned. I rarely convert anyone to the church of surfing, though I do feel evangelical at times."

Bruce Weber

Robert Weaver (nickname Wingnut) is a former pro surfer who is endlessly intrigued by the wealthy people he guides on glamorous surf trips around the globe. "On a mountain you can do it again and again until you get it right," he says. "With the ocean, every wave is different. The tides, winds, and swell change in minutes out there. It's a shifting dynamic that makes it all the more fun when you succeed."

Wingnut, who charges his clients $2,500 per day of surfing, is an expert in the psychology of this particular group. "The bankers have conquered every other sport; they want to try this one. Then they find out it's much harder than they thought, and it's good for them. I have clients who try it for the first time in their forties, then fall in love with the challenge, the environment, the people. Suddenly they're tired of paying for lift tickets and standing in lines."

Just so you understand the kind of surf instructor the wealthy are hiring to come along on their trips: Securing Wingnut to surf with you is like hiring champion alpine racer Franz Klammer to ski with your family. David Sokolin, president of Sokolin Wines, one of the largest retailers of rare wines in the world, has been invited on trips on which Wingnut served as surf guide and lifeguard to a gang of rock stars and hedge-funders. Sokolin compares hiring Wingnut to hiring a surfing Harlem Globe-trotter: "He has been seen on a board upside down in a headstand, often mooning the entire group." I've tried—unsuccessfully thus far—to score an invite on one of these boys' surfing trips to an exotic locale. Sokolin's reason for my being rejected: "There's a certain dynamic when 10 guys are hanging out alone. You put one woman in there and it could change the whole fratlike environment. It's amazing how much a bunch of 40-year-old guys start acting like teenagers with no supervision."

I was lucky enough to surf with Wingnut once, on a guided boat trip in the Maldives. In the middle of a stormy Indian Ocean, a rattan bistro chair floated by us. I turned to him and said, "I dare you." He winked, grabbed the chair, and paddled out holding the chair's lower bar to the board with his chin. He proceeded to catch the very next wave—you guessed it—seated on the chair, pretending to sip some tea.

"The work hard/play hard guy whose party days are waning may be looking for a new way of expressing that drive and release," says Charles Fulford, group creative director at Huge Inc., a digital products company. Fulford has perfected the alchemy of a trip filled with all-day surfing followed by tacos and tequila at night. The surfers hiring a pro like Wingnut are, unsurprisingly, not satisfied with mastering the waves in easy-to-get-to and well-known Malibu; they're looking for the greatest surf breaks on planet Earth, and they want to master them. "It can be a grueling sport, and in order to advance, it takes a lot of dedication," Fulford says. "But look at the explosion in triathletes over the last few years. It's really about self-competition."

The trend of power brokers challenging themselves mentally and physically, sometimes in harsh conditions, isn't necessarily new, but the surfing angle may be. We all remember when a group of New York A-listers made a disastrous attempt to climb Mount Everest. The bare-bones Ashram retreat charges $5,000 a week for a no-frills recharge. Clients endure spartan meals and arduous hikes in the name of detoxing but also as a sign of inner toughness, a badge that says money hasn't made them soft.

Tony Caramanico, a surf guide who takes publishing, media, and financial types to breaks in St. Bart's and Tobago (where he has a home), says, "There is surf all over the world, in weird places you wouldn't expect, like Egypt, Japan, Vietnam. There's a certain adventure in surfing that leads to what we call feeling 'stoked.' Stoked is the sense you get riding a wave, when you feel elated but drained. You get that smirk on your face that says you're so happy with what you just did. It doesn't affect other people. You're just happy for yourself." An added benefit: These days, when people's eyes are glued to screens 18 hours a day, there's no pocket for your phone out on the water.

Bruce Weber

Sokolin points out that having the wherewithal to surf the world's best places doesn't mean anything once you put your body in the water. "These guys might be initially attracted because it looks cool or they would like to envision themselves as laid-back guys enjoying nature," he says. "But the ones who stick with it are pretty much like any other surfer, despite pulling up to the beach in a Mercedes G wagon."

Most of the time, anyway. Wingnut admits that there is a period of acclimation to the local culture—and to the mellow culture of surfing overall—when he takes clients to far-off spots. "New Yorkers have a personality type that doesn't deal well with service people and with certain issues on timing. I have to constantly remind them, 'Hey, you're in Mexico. There's a certain pace here.' "

For those who insist on having accommodations and service on a par with their high-end expectations, a few resorts have risen to meet the challenge. Tropicsurf offers packages at various resorts for people seeking a high level of comfort but with virgin waves and paid surf guides giving them undivided attention. The company's Maldives locations have offshore trade winds that make the waves consistent and smooth as glass, regular swells that pump out large waves, and breaks for all ability levels.

The Nihiwatu resort on Sumba, in Indonesia, was recently bought and overhauled by Chris Burch, the New York entrepreneur who co-founded Tory Burch and C. Wonder. The property also happens to sit atop one of the best left breaks in the world—and the waves are reserved for hotel guests only. The pop star Pink can sometimes be found here, as can William van Cutsem and his wife Rosie (a.k.a. Prince William and Kate Middleton's closest friends), as well as Jawbone designer Yves Béhar and Place Vendôme jeweler Lorenz Bäumer.

When I visited the hotel (it took me four days to reach it, starting from Manhattan), a host of glamorous Europeans had taken it over. No question they were serious surfers. Halfway through my visit, communal meals on the veranda became strained: A cosmetics CEO and a banking scion didn't speak for 48 hours because part of the group had snuck out at 6 a.m. to battle a glassy 12-foot swell without inviting the others.

No one wants to miss any of the action on Sumba, known for its glorious bungalows, waterfalls, and spa safaris. Surfing heaven and luxury mecca combined, in other words. A big chunk of the resort's profits (as well as the guests' generosity) helps feed kids in the island's schools, dig wells, and buy books. Because of these efforts, Burch says, "there's a high degree of respect for our guests. Our wave is particularly private, and locals make sure guests get first shot at it." Eva Guerrand-Hermès, a former Harvard varsity tennis player and co-owner of the LOLE brand of women's athletic gear, often visits Nihiwatu. She says she is lured back by the opportunity to surf in distant, unpopulated places. "You've gone to the end of the world," she says, "to lift yourself to another place through this sport."

How do hardcore locals feel about this invasion of bankers and rock 'n' rollers? Doesn't it decrease their stoke? For sure, many don't welcome the newcomers—although, Wingnut says, the best surfers are mostly concerned with everyone's safety, and they give each other proper right of way and respect. Charles Fulford says that somehow the water, and its ability to disconnect us from every hassle on land, has a way of serving as an equalizing force, no matter where you come from or what you do. "Many breaks may now have a few people coming from high finance," Fulford says, "but anyone who lumps every person that works in a specific sector into a set personality type doesn't get surfing. They're the one with a bad vibe."

Holly PetersonHolly Peterson is the author of The Idea of Him and the New York Times bestseller The Manny.

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